Randy — very well-written and good points.
One thing, without question, that the Bay Area (and to some extent, Seattle) has, and that Portland does not, is a LOT of ready-to-invest money. As in, multiple billion-dollar-plus funds. In Portland, I think there are far more potentially-great companies being founded than there is money to fund them adequately.
I’ve been on both sides of this — both raising in Portland, and in attending investor pitches as you describe. On the raise side, I’ve felt the frustration of pitching and wondering if there’s even any investable money in the group. Time is the most precious commodity for an entrepreneur, and it’s terribly frustrating to invest time in something that goes nowhere. (Granted, we were raising in 2011, when there was probably even less money to go around, but probably fewer companies raising, too.)
On the other side, attending an investor group, I would literally see 4 pitches in an evening, and could imagine investing, or at least doing due-diligence, in all 4 of them. Yet, I don’t have unlimited funds to invest, so I would wind up passing on all of them.
I’m not sure where that leaves Portland, or what the answer is. But I feel you, and would be happy to participate in the conversation if I can help in any way.